It is known in the art that the polymerization of isobutylene and isobutylene copolymers can be initiated with combinations of dialkylaluminum halides and active organic halides, e.g. see J. P. Kennedy, pages 302 ff, and in particular pages 306 and 307 of Polymer Chemistry of Synthetic Elastomers, edited by J. P. Kennedy and E. G. M. Tornqvist, Part I, Interscience New York, 1968. Kennedy shows that the most reactive organic halide is tertiary-butyl chloride (TBC). In terms of a parameter called "cocatalyst efficiency, g/mole" he shows TBC with a value of 1,030,000 compared, for example, with a value of 369 for secondary-butyl chloride. Kennedy shows that allylic halides and benzylic halides are relatively active with cocatlyst efficiencies in the range of about 7,000 to 140,000.
Diem et al attempted to utilize adamantyl iodide in the presence of UV light to induce the polymerization of isobutylene. No polymer was produced upon irradiation of isobutylene, adamantyl iodide (AI) or TBC. The addition of zinc dust gave low yields of polyisobutylene having a low molecular weight. Diethyl zinc had no influence. See Diem, T., Kennedy, J. P. et al, "Isobutylene Polymerization in The Presence of UV Light, Organic Iodides and Zinc Iodide," Polymer Bulletin 1, 281-285 (1979). Diem also reacted adamantyl iodide with diethylaluminum iodide (mol ratio AlEt.sub.2 I/AD-I, 5/1) in the dark with isobutylene and obtained 0.73% conversion to polymer at -70.degree. C. (ibid p. 284, Table II).
Relative solvolysis rates in 80% ethanol at 25.degree. C. are reported by Carey, F. A. and R. J. Sundberg, Advanced Organic Chemistry, Second Ediion, Part A, Plenum Press, New York, 1984, page 261. The relative solvolysis rates for tertiary-butyl bromide and 1- bromoadamantane are 1 and 0.001 respectively. The research of Kennedy (loc cit) suggests that halide reactivity is a measure of catalyst reactivity. On this basis, it would not be anticipated that haloadmantanes would be useful in preparing active catalyst systems.